Indole-2-carboxylic acid → HCID 44450783, compound

HRID 651115Notes

Reaction equation

HRID 651115 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:4]([N:6]1[CH2:11][CH2:10][CH:9]([OH:12])[CH2:8][CH2:7]1)=[O:5].[NH:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[C:21]1[C:29](O)=[O:30]>>[CH2:13]([C@H:3]([NH:2][C:29]([C:21]1[NH:20][C:28]2[C:23]([CH:22]=1)=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:30])[C:4]([N:6]1[CH2:11][CH2:10][CH:9]([OH:12])[CH2:8][CH2:7]1)=[O:5])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 72899Indole-2-carboxylic acidHCID 69688479HCID 69688479, compound

Product 1

HCID 44450783HCID 44450783, compound

Procedure

(S)-2-Amino-1-(4-hydroxy-piperdin-1-yl)-3-phenyl-propan-1-one hydrochloride (3.4 mmol) and 1H-indole-2-carboxylic acid (3.7 mmol) were coupled according to Procedure A (0-25° C. reaction temperature, 48 hour reaction time). The product was purified by chromatography on silica gel eluted with 50, 75 and 100% ethyl acetate in hexanes, followed by trituration with 1:1 ether-hexanes. Yield 1.14 g, 88%; HPLC (60/40) 3.52 minutes (98%); PBMS 392 (MH+, 100%);

Workup

  1. customThe product was purified by chromatography on silica gel
  2. washeluted with 50, 75 and 100% ethyl acetate in hexanes
  3. customHPLC (60/40) 3.52 minutes (98%)

Sources & evidence

ORD record
ord-9c8c6981eefd4a2a8f88bdbc11a0b7a4
Source dataset
uspto-grants-2001_08
Patent number
US06277877B1

Reaction notes

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